Hierarchy of Metabolic Compounds Based on Their Synthesizing Capacity Thomas Handorf1
Oliver Ebenh¨ oh1
Daniel Kahn2
Reinhart Heinrich1
[email protected] 1 2
Theoretcial Biophysics, Institute of Biology, Humboldt Unversity Berlin, Germany Institut National de la Recherche Agronomique, Toulouse, France
Keywords: metabolic networks, scope, scope hierarchy, structural analysis
1
Introduction
With the emergence of biochemical databases such as KEGG or Brenda, information about largescale metabolic networks became easily accessible. Several approaches for the structural analysis of metabolic networks have been introduced, such as flux balance analysis, the concept of elementary flux modes or extreme pathways, as well as graph theoretical analyses. Recently, we introduced a new approach of network analysis based on the concept of scopes [1]. This method allows to determine all compounds which can in principle be synthesized from a given set of substrates using a specified set of biochemical reactions.
2
Method and Results
Starting with given metabolites, called seed compounds, the algorithm selects from a database in an iterative manner those reactions whose substrates are either part of the set of seed compounds or are products of reactions which were already selected in an earlier iteration step. This network expansion process ends when no further reactions fulfilling this condition can be found. All metabolites which can be produced by the resulting set of reaction form the scope of the seed compounds. Scopes describe therefore the synthesizing capacity of the corresponding seed compounds in a specified metabolic network. In this work we confine ourselves on scopes of individual metabolites, which means that for each expansion process only one compound is used as seed. We systematically calculated the scopes of 4104 compounds included in the KEGG database. As mentioned in [1] different seed compounds may have identical scopes leaving only 2922 distinct scopes. A scope may be included in another scope. If the scope of compound B, Σ(B), is a proper subset of the scope of A, Σ(A), then Σ(A) is a superscope of Σ(B) and Σ(B) is a subscope of Σ(A). There exists nesting in the sense that for three compounds A, B, C the relation Σ(C) ⊂ Σ(B) ⊂ Σ(A) holds. This inclusion relations can be compiled into a directed acyclic graph, where nodes represent the distinct scopes. Directed edges point from superscopes to their subscopes, where in case of nesting as described above the edge between node A and C is omitted. Figure 1 shows the largest connected component of this graph for the analysed biochemical network. This component contains the most relevant information as the other nodes are either isolated or connected to only very few other nodes. Edges always point in downward direction. Therefore nodes near the bottom of the graph represent small scopes which only have a small number of subscopes, while larger scopes are situated rather at the top. Remarkably, the nodes of the graph differ strongly with respect to both, their in and out degree. A node has a large out degree (mushroom shaped structures) if its scope contains many different
4-Methylene-L-glutamine(1)
Ricinine(1) 2-Succinylbenzoyl-CoA(1)
1,4-Dihydroxy-2-naphthoate(1) Deisopropyldeethylatrazine(1)
Reduced ferredoxin(1)
Reduced coenzyme F420(1) HSO3-(1)
Oxidized ferredoxin(1)
Coenzyme F420(1)
4-Sulfocatechol(3) Xanthopterin-B2(1)
N-(Aminomethyl)urea(1) (R)-2-Ethylmalate(1)
N-(Hydroxymethyl)urea(1)
Ferrocytochrome c3(1)
Ferricytochrome c3(1)
5,10-Methylenetetrahydromethanopterin(1)
5-Formyl-5,6,7,8-tetrahydromethanopterin(2)
beta-Alanyl-CoA(1) trans-1,3-Dichloropropene(7)
Phytoene(3)
Hydrogen(2)
4-Methylene-L-glutamate(1)
Neurosporene(1)
Deethylatrazine(1)
3-Carboxy-4-methoxy-N-methyl-2-pyridone(1) 4-Trimethylammoniobutanal(1)
Thiourocanic acid(1)
(5Z,8Z,11Z,14Z)-Icosatetraenoic acid(23)
Leukotriene C4(1)
Leukotriene D4(2)
Leukotriene E4(1)
Methylenediurea(2)
2-Chloro-4-hydroxy-6-amino-1,3,5-triazine(1) N-Acetyl-D-muramoate(1)
Crotonoyl-CoA(6)
3-(Uracil-1-yl)-L-alanine(1) Dethiobiotin(1) 2-(Hydroxymethyl)-4-oxobutanoate(1)
Ethylamine(1)
3-Hydoxy-4-oxo-4H-pyrid-4-one(1) Biotin amide(1)
Protoanemonin(2)
Biotin(1) D-Galactosyl-3-N-acetyl-beta-D-galactosamine(1)
Spirodilactone(1) Hercynine(1) Isopropylamine(1) Phenol sulfate(1) 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine(1) N-Ethylglycine(1)
Chloroacetic acid(1)
2,2-Bis(4'-chlorophenyl)ethanol(3)
4,4'-Dichlorobenzophenone(1)
N-Acetylmuramoyl-Ala(1) 4-Chlorocatechol(8)
Bis(4'-chlorophenyl)methane(1)
(S)-2-Amino-3-(3-hydoxy-4-oxo-4H-pyridin-1-yl)propanoate(1)
Selenohomocysteine(2)
D-Galactosyl-3-(N-acetyl-beta-D-galactosaminyl)-L-serine(1)
Selenide(1)
Hydroxyatrazine(1)
N-Isopropylammelide(1)
O-Acetylhomoserine(1)
Kaempferol 3-O-beta-D-glucosyl-(1->2)-beta-D-glucoside(1) O-Acetyl-L-homoserine(1)
Methylmalonate(2)
N5-Ethyl-L-glutamine(3)
1-Chloro-2,2-bis(4'-chlorophenyl)ethane(1)
Methaneselenol(1)
O-Succinylhomoserine(1)
Ergothioneine(1)
Selenomethionine(1)
(S)-2-O-Sulfolactate(1)
Selenocystathionine(1)
Thiocyanate(1)
Carbonyl sulfide(1)
1,1-Dichloro-2,2-bis(4'-chlorophenyl)ethane(1) 1-Chloro-2,2-bis(4'-chlorophenyl)ethylene(1) Proclavaminic acid(1)
1,1-Dichloro-2,2-bis(4-chlorophenyl)ethylene(3) 2-(4'-Chlorophenyl)-3,3-dichloropropenoate(1)
Cyclohexanone(1) Cyclohexylsulfamate(1)
2-Hydroxy-3-chloropenta-2,4-dienoate(1)
Cyclohexylamine(1) Dihydroclavaminic acid(1)
Monomethyl sulfate(1)
Guanidinoproclavaminic acid(1) Clavaminic acid(1)
S-Glutathionyl-L-cysteine(1) Sulfoacetaldehyde(1)
Sulfate(5) Deoxyguanidinoproclavaminic acid(1)
Formyl-CoA(1)
H2S2O3(1) 4-Deoxy-beta-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine(1) S-Sulfo-L-cysteine(1)
4-Deoxy-beta-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine4-sulfate(2) Hydrogen sulfide(1)
Taurocyamine(2) 3-Sulfopyruvate(1)
Cl-(1)
Se-Adenosylselenohomocysteine(1)
Lactoyl-CoA(3)
Succinate semialdehyde(1)
Glutamate(1)
Methanethiol(1) 2-Methylacetoacetyl-CoA(1) L-Cysteate(1)
Cyanide(1) 3-Hydroxy-3-methylglutarate(1)
Demethylisoalangiside(1) (1-Hydroxycyclohexan-1-yl)acetyl-CoA(1)
Alanine(1)
2-Hydroxy-3-oxoadipate(1)
Trimethylamine N-oxide(1) Triacetate(2)
Secologanin(1) (E)-Glutaconate(1)
Propanoyl-CoA(1) Acetyl-CoA(16) 3-Oxoadipyl-CoA(1) Lochnerinine(1) Glutaconyl-1-CoA(2) Parathion(1)
2-Oxoglutarate(2)
(S)-3-Hydroxy-3-methylglutarate(1) Demethylalangiside(1)
Diethylthiophosphoric acid(1)
3-alpha(S)-Strictosidine(5)
Paraoxon(1)
2-Oxohept-3-enedioate(6)
4-Coumarate(3)
4-Hydroxystyrene(1)
3,4-Dihydroxystyrene(1)
N,N-Dimethylformamide(1)
Dimethylamine(1)
5-Aminoimidazole(1)
Imidazol-5-yl-pyruvate(1)
N-Formiminoglycine(2)
1H-Imidazole-4-ethanamine(1) Imidazole-4-acetate(1)
Diethylphosphoric acid(1)
3,5-Dichlorocatechol(6) Aminoparathion(1)
2-Nitropropane(1) Imidazole-4-acetaldehyde(1)
(S)-Norcoclaurine(1) Vitexin(2) Phenethylamine(1) 4-Hydroxybenzoyl-CoA(1) Malonate(1)
L-Cystine(1)
N-Acetyl-L-glutamate 5-semialdehyde(1)
(S)-Norlaudanosoline(2)
3,4-Dihydroxyphenylacetaldehyde(1)
Barbiturate(1) Kaempferol(1)
1,1,1-Trichloro-2,2-bis(4-chlorophenyl)ethane(2) Sulfur dioxide(1)
2-Phenylacetamide(1)
trans-4-Hydroxy-L-proline(5)
4-(2-Aminophenyl)-2,4-dioxobutanoate(2)
cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide(4)
NH3
2-(Hydroxymethyl)-3-(acetamidomethylene)succinate(1)
Atrazine(2) Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide](1)
Thiocysteine(1) Acrylamide(2)
Ornithine(1)
HCl(1)
Betaine(1) Pelargonidin(1)
N-Methylhydantoin(1)
Cysteine(1) PQQH2(1)
Naringenin(7)
3-Oxopropanoate(2) Phenylacetic acid(1)
2-Propyn-1-ol(1) Mercaptoethanol(1) NG,NG-Dimethyl-L-arginine(1)
Dihydrokaempferol(1)
4-Hydroxy-L-glutamate(1)
Apigenin(1)
gamma-Hexachlorocyclohexane(4)
Mercaptopyruvate(1) Glutathione(16)
Kaempferol3-O-beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside(1)
gamma-Glutamyl-beta-aminopropiononitrile(1)
cis-3,4-Leucopelargonidin(1)
4-Methylthio-2-oxobutanoic acid(1) 3-Butyn-1-ol(1)
Kaempferol3-O-[6-(4-coumaroyl)-beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside](1) Cystine(1)
Oxalyl-CoA(1)
L-Aspartylhydroxamate(1)
3-Indoleglycolaldehyde(1)
2,5-Dichloro-2,5-cyclohexadiene-1,4-diol(1)
4-Nitrocatechol(2)
2,5-Dichlorophenol(1)
(5-L-Glutamyl)-L-glutamate(1)
Quercetin 3-O-[beta-D-xylosyl-(1->2)-beta-D-glucoside](1)
D-4-Hydroxyphenylglycine(1)
Homocystine(1) Quercetin 3-O-(6-O-malonyl-beta-D-glucoside)(1)
2-Amino-4-oxopentanoic acid(1)
gamma-Amino-gamma-cyanobutanoate(1)
2-Hydroxybutane-1,2,4-tricarboxylate(3)
alpha-Aminopropiononitrile(1)
PQQ(1) Quercetin 7-O-beta-D-glucoside(1) 3-Methylthiopropanamine(1)
1,2,4-Trichlorobenzene(1)
1,2-Dichloroethane(1)
2-Chloroethanol(1)
3,4,6-Trichlorocatechol(2)
2,5-Dichloro-carboxymethylenebut-2-en-4-olide(2)
3-Chloro-D-alanine(3)
Pelargonidin 3-O-(6-O-malonyl-beta-D-glucoside)(1)
gamma-L-Glutamyl-D-alanine(1)
Homocysteine(1) 5-Aminolevulinate(4) L-Glutamate(146)
Vitexin 2''-O-beta-L-rhamnoside(1) Cyanidin 3-O-(6-O-malonyl-beta-D-glucoside)(1)
3-(3,4-Dihydroxyphenyl)pyruvate(1)
L-2-Amino-3-oxobutanoic acid(1) 2,3-Dihydroxy-4'-chlorobiphenyl(2)
alpha-Amino-gamma-cyanobutanoate(1) Pelargonidin 3-O-rutinoside(1)
3,4-Dihydro-2H-Pyrrole-2-carboxylate(1)
Glycocholate(2) beta-Aminopropionitrile(1)
104-1(1) Pelargonidin 3-O-rutinoside 5-O-beta-D-glucoside(1)
SO2(1)
S-Benzoate coenzyme A(1)
4,5-Dioxopentanoate(1) 3-Methyldioxyindole(1)
Cyanidin 3-O-rutinoside 5-O-beta-D-glucoside(1) 3-Sulfinylpyruvate(1) Quercetin 3-O-beta-D-glucosyl-(1->2)-beta-D-glucoside(1)
2,3-Dihydroxy-p-cumate(3)
L-erythro-4-Hydroxyglutamate(1) 3-Vinylcatechol(2)
2-Butenoate(1)
L-4-Hydroxyphenylglycine(1)
2-Aminomalonate semialdehyde(1) Anthranilyl-CoA(1)
Butanoylphosphate(1) L-Lysine(14)
Hypotaurine(2)
L-Isoleucine(1)
2-Methylpropanoate(1)
Hydroxymethylbilane(4)
gamma-L-Glutamyl-L-cysteine(1) N-Acetylneuraminate(2)
N6-D-Biotinyl-L-lysine(1)
5'-Butyrylphosphoinosine(1)
3-Methyl-2-oxopentanoate(1)
Glycochenodeoxycholate(1)
2-Hydroxyglutarate(1)
Dimethylmaleate(7)
Aniline(1) Tyramine(2) L-2,3-Dihydrodipicolinate(1) L-Aspartate 4-semialdehyde(1) N-Acetyl-L-glutamate(1)
N1-Acetylspermine(1)
Acetone cyanohydrin(1) 3-Aminopropanal(1)
Hexadecenal(1)
1-(4-Hydroxyphenyl)-2-(methylamino)ethanol(1) 4-Hydroxymandelonitrile(1)
Tetrangomycin(2)
Sphingosine(1)
5-Methoxytryptamine(1)
Urdamycinone B(1)
N-Methyl-L-glutamate(1) 4-Guanidinobutanal(1)
6-Hexanolide(3)
Hexadecanal(1)
Selenocysteine(3)
Feruloyl-CoA(2)
L-Proline(4)
Sphinganine 1-phosphate(2) Homoeriodictyol(1)
Sphinganine(1)
Estrone 3-sulfate(1)
Glucobrassicin(1) N-((R)-Pantothenoyl)-L-cysteine(1)
Chlorobenzene(1)
N-Acetyl-beta-D-glucosaminylamine(1)
L-Glutamate 5-semialdehyde(2)
Aminoacetaldehyde(1)
2-Oxobutanoate(1)
Phenylacetaldehyde(2)
Pantetheine(1) 3beta-Hydroxyandrost-5-en-17-one 3-sulfate(1)
4-Aminobutanoate(1) Strictosidine aglycone(11)
2,5-Dioxopentanoate(5)
2-Oxoarginine(1)
Beta-1,2,3,4,5,6-hexachlorocyclohexane(3) 4-Hydroxyphenylacetaldehyde(1) 5-Aminopentanamide(1)
5-Oxopentanoate(1) Adenosine(10)
N-Succinyl-2-L-amino-6-oxoheptanedioate(1)
Methyloxaloacetate(1) Glycoprotein phospho-D-mannose(1) 4-Acetamidobutanoate(1) Hexanoic acid(1)
Phenol(1)
2-Succinylbenzoate(2) Salicylate(1)
Urethane(1)
Cyanin(1)
N-Acetyl-L-2-amino-6-oxopimelate(1)
Glycoprotein N-acetyl-D-glucosaminyl-phospho-D-mannose(1)
4-Hydroxybenzoate(3)
N2-Acetyl-L-aminoadipate semialdehyde(1)
N-Methylhexanamide(1)
2-Hydroxyphenylacetate(1)
L-Pipecolate(3)
N-Acetyl-beta-alanine(1)
2,3-Dihydro-2,3-dihydroxybenzoate(1)
Pentanamide(1)
Pentanoate(1)
Cyanidin 3-O-(6-O-p-coumaroyl)glucoside-5-O-glucoside(1) Cyanidin 3-O-(6-O-p-coumaroyl)glucoside(1)
2-Propyn-1-al(1)
6-Acetamido-2-oxohexanoate(1)
Phenylpyruvate(7)
5-Acetamidopentanoate(1)
4-Chlorobenzoate(2)
Aspirin(1) NH3(6)
Shikimate(1)
1-Methylpyrrolinium(2)
3-Butyn-1-al(1)
Cadaverine(1)
Nitrogen(1)
Chloride(2)
Blasticidin S(1)
Dichloromethane(1) N-Methylputrescine(1)
L-Carnitinamide(1)
Ethanolamine(4)
Deaminohydroxyblasticidin S(1)
L-Carnitine(2)
Glutathionylspermidine(1) 4-Chlorophenylacetonitrile(1) N-Methylhistamine(1)
Methylimidazole acetaldehyde(1)
3-Isochromanone(1)
3-Methoxy-4-hydroxyphenylacetaldehyde(1)
6,7-Dimethyl-8-(1-D-ribityl)lumazine(1)
Styrene(3)
Benzoyl acetate(1)
3-Methoxytyramine(1)
N-Feruloylglycine(1) 3-Ketolactose(1)
4-(1-D-Ribitylamino)-5-amino-2,6-dihydroxypyrimidine(1)
beta-D-Galactose(1)
Chenodeoxycholoyltaurine(2)
Reduced riboflavin(1)
Taurocholate(2)
4-Chlorobenzoyl-CoA(1)
3-Keto-beta-D-galactose(1)
Coproporphyrinogen I(1)
3,5-Dibromo-4-hydroxybenzonitrile(1)
4-Chlorophenylacetate(1)
3,5-Dibromo-4-hydroxybenzoate(1)
Propenoate(1)
Acetamide(1)
L-Rhamnonate(4) Propanoate(1)
1-(4-Hydroxy-2-methylpyrimid-5-ylmethyl)-3-(beta-hydroxyethyl)-2-methylpyridinium bromide(1)
Cyanidin 3-O-glucoside(1) 1-(4-Amino-2-methylpyrimid-5-ylmethyl)-3-(beta-hydroxyethyl)-2-methylpyridinium bromide(1)
Formamide(2)
Spermine(1)
Acetone(1)
FADH2(1) Cobinamide(1)
Berberine(4)
Sorbose(1) 5-Oxoproline(1)
Cobyrinate(2)
N-Acetyl-D-glucosamine(4)
Acetophenone(2)
Renilla luciferin(1)
S-Adenosylmethioninamine(1)
Oxidized Renilla luciferin(1)
Reduced FMN(1) Bromochloromethane(1)
FAD(1) Anisole(1)
5-Aminopentanoate(1) Cypridina luciferin(1)
3-Ketosucrose(1)
Pantothenate(1)
Ethanol(1)
FMN(1)
Oxidized Cypridina luciferin(1)
6-Amino-2-oxohexanoate(2) Watasenia luciferin(1)
Guaiacol(1)
(S)-Reticuline(2)
hn(1)
Riboflavin(1) N4-Acetylaminobutanal(1)
Tetracenomycin F2(2)
L-Normetanephrine(1)
3-Methoxy-4-hydroxyphenylglycolaldehyde(1)
Oxidized Watasenia luciferin(1)
4-Dedimethylamine-4-oxo-anhydro-7-Cl-tetracycline(1)
L-Sorbose(2)
Decarboxytetracenomycin F1(1)
N-Methyltyramine(1)
D-Fructose(1) L-Homoserine(1)
Tetrahydropalmatine(1) 4-Hydroxy-3-methoxy-benzaldehyde(3) 2-Aminobutan-4-olide(1)
Deoxycytidine(1)
Chenodeoxycholate(1)
Deoxyribonolactone(1)
(E)-3-(Methoxycarbonyl)pent-2-enedioate(1)
(E)-2-(Methoxycarbonylmethyl)butenedioate(1)
Ferulate(2)
N-Acetylputrescine(1) Tetracenomycin M(1)
Taurine(1)
4-Hydroxybutanoic acid(1)
Formate(1) L-Metanephrine(1)
Estrone(1) L-2-Methyltryptophan(1) S-Adenosyl-L-methionine(4)
Methylamine(1)
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate(3)
3beta-Hydroxyandrost-5-en-17-one(1) Deoxyuridine(1)
N-Methylanthranilate(1) D-Glucose 6-sulfate(1)
Benzene(1)
5-Methylthio-D-ribose(1)
4-Aminobutanal(1)
(R)-Pantoate(1) 2-Decarboxytetrangomycin(1)
Putrescine(1)
Se-Propenylselenocysteine se-oxide(1)
S-Methyl-L-methionine(1)
Homospermidine(1) Tetrachloroethene(5)
Bis(3-aminopropyl)amine(1)
Vinblastine(2) Lumichrome(1)
N-Sulfo-D-glucosamine(2)
3-(2-Aminoethyl)-1H-indol-5-ol(2)
Propanoyl phosphate(1)
S-Inosyl-L-homocysteine(1)
N1-Acetylspermidine(1)
Propinol adenylate(1)
(S)-beta-Methylindolepyruvate(1)
Carnitine(2)
2-Methylcholine(1)
Bromide(1) N,N-Dimethylaniline N-oxide(1)
Acrolein(1)
Haloacetate(1)
Halide(1)
(S)-N-Methylcoclaurine(2) cis-1,2-Dihydro-3-ethylcatechol(1)
5-Hydroxyindoleacetaldehyde(2)
Vindoline(1)
N-Methylaniline(1)
Palmatine(1) Styrene cis-glycol(1) Nicotianamine(1)
Co-Methyl-Co-5-hydroxybenzimidazolylcob(I)amide(1) 5-Hydroxy-L-tryptophan(3)
Formaldehyde(2)
Heptadecane(1)
3-Hydroxypropanoate(1)
3-Methylindolepyruvate(1)
Methyl(2E,6E)-(10R,11S)-10,11-epoxy-3,7,11-trimethyltrideca-2,6-dienoate(1)
Octadecanal(1)
Quinone(9)
Hippurate(2) (S)-Coclaurine(1)
Orsellinate(2)
Protoporphyrinogen IX(2)
Orcinol(1)
5,6-Dihydrothymine(2) Hordenine(1)
2-Indanone(1)
Stipitatonate(1) Spermidine(1)
Carbamoyl phosphate(2) (S)-Nororientaline(1) Deoxyadenosine(1) (S)-3'-Hydroxycoclaurine(1) 2,5-Diamino-6-hydroxy-4-(5'-phosphoribosylamino)-pyrimidine(1)
3-Oxododecanoic acid(1)
1,3-Diaminopropane(1) Vicianose(1)
S,S-Dimethyl-beta-propiothetin(1)
Dimethyl sulfide(1)
(S)-Norreticuline(1)
4-Amino-3-hydroxybutanoate(1)
2-Hexaprenyl-6-methoxyphenol(2)
3-Octaprenyl-4-hydroxybenzoate(1)
2-Octaprenylphenol(1)
Lipopolysaccharide(1)
N(pai)-Methyl-L-histidine(1) (R)-Vicianin(1)
2-Undecanone(1)
3-Hydroxy-L-glutamate(1)
3-Hexaprenyl-4-hydroxy-5-methoxybenzoate(1)
5-Hydroxybenzimidazolylcobamide(1)
(R)-Mandelamide(1) beta-Alanyl-N(pai)-methyl-L-histidine(1)
Stipitatate(1)
beta-Alanine(1)
UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine(1) N-Methyltryptamine(1)
(S)-6-O-Methylnorlaudanosoline(1)
N-Acetylanthranilate(1)
3-Deoxyoctulosonyl-lipopolysaccharide(1)
2-Methylquinoline-3,4-diol(2) 3-Deoxy-D-manno-octulosonate(1)
3-(Hydrohydroxyphosphoryl)pyruvate(1) 1-Carboxyvinyl carboxyphosphonate(1) 4-Chlorophenol(1)
(R)-Prunasin(2)
4-Chlorophenoxyacetate(1) CO2(10)
N-Benzyloxycarbonylglycine(1) 2,4,5-Trichlorophenoxyacetic acid(1) 5-Methylcytosine(1)
L-Threonine O-3-phosphate(1)
2,4,5-Trichlorophenol(1)
D-1-Aminopropan-2-ol O-phosphate(1)
Activated methyl group(1) UDP-N-acetylmuramate(1)
Tetracenomycin D3(1)
N-Trimethyl-2-aminoethylphosphonate(1)
Tetracenomycin D1(1)
N-Dimethyl-2-aminoethylphosphonate(1) (R)-4-Dehydropantoate(1)
Tetracenomycin B3(1)
5-Dehydro-D-gluconate(1)
Tetracenomycin X(1)
D-Ribitol 5-phosphate(1)
10-Carboxy-13-deoxycarminomycin(1)
(R)-3,3-Dimethylmalate(1)
Sugar phosphate(1)
Tetracenomycin B1(1)
Tetracenomycin A2(1)
13-Deoxycarminomycin(1)
Sugar(1)
5-Hydroxykynurenamine(1) (R)-3-Hydroxybutanoate(2)
Caldesmon phosphate(1)
Caldesmon(1)
5-Hydroxyindolepyruvate(1) D-Sorbitol 6-phosphate(1)
Sorbitol 6-phosphate(1)
(R)-5-Phosphomevalonate(1)
Streptomycin 6-phosphate(1)
7,8-Dihydroxykynurenate(3)
[Acetyl-CoA carboxylase] phosphate(1)
(-)-trans-Isopiperitenol(1)
(R)-5-Diphosphomevalonate(1)
Sorbitol(1)
Streptomycin(1)
[Acetyl-CoA carboxylase](1)
[Pyruvate dehydrogenase (lipoamide)] phosphate(1)
[Pyruvate dehydrogenase (lipoamide)](1)
[3-Methyl-2-oxobutanoate dehydrogenase (lipoamide)] phosphate(1)
[3-Methyl-2-oxobutanoate dehydrogenase (lipoamide)](1)
D-Ribose 1,5-bisphosphate(1)
3,4-Dihydroxyphenylacetate(2)
Cholesta-5,7-dien-3beta-ol(4)
Phosphorylase a(1)
Phosphorylase b(1)
[Glycogen-synthase D](1)
[Glycogen-synthase I](1)
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate(2) (2E,6E)-(10R,11S)-10,11-Epoxy-3,7,11-trimethyltrideca-2,6-dienoicacid(1)
1-Phospho-alpha-D-glucuronate(1) Benzonitrile(2)
Monoterpenol(1)
3-(2-Hydroxyphenyl)propanoate(2) 3-Aminoisobutanoate(1)
Monoterpenyl diphosphate(1)
Undecaprenyl phosphate(1)
3-(3,4-Dihydroxyphenyl)lactate(1) UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanine(1)
Undecaprenyl diphosphate(1)
3-(ADP)-glycerate(1)
UDP-N-acetylmuramoyl-L-alanine(1) 3-(ADP)-2-phosphoglycerate(1)
1-Aminopropan-2-ol(1)
1-Amino-1-deoxy-scyllo-inositol(1) [Pyruvate kinase] phosphate(1)
[Pyruvate kinase](1)
6-Phospho-2-dehydro-D-gluconate(1) Myosin light-chain phosphate(1)
Myosin light chain(1)
7,8-Dihydro-7,8-dihydroxykynurenate(1) 2-Carboxy-D-arabinitol 1-phosphate(1)
2-Carboxy-D-arabinitol(1)
1,2-Didehydropiperidine-2-carboxylate(1) S-Methyl-3-phospho-1-thio-D-glycerate(1)
S-Methyl-1-thio-D-glycerate(1)
[Hydroxymethylglutaryl-CoA reductase (NADPH)] phosphate(1)
[Hydroxymethylglutaryl-CoA reductase (NADPH)](1)
3-(Imidazol-4-yl)-2-oxopropyl phosphate(2)
1-Amino-1-deoxy-scyllo-inositol 4-phosphate(1)
1D-myo-Inositol 1,3,4,5,6-pentakisphosphate(1) beta-Aminopropion aldehyde(1) 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-al(1) D-Glucosamine(3) dUDP(1)
NH4OH(1) (R)-Acetoin(2) Glycol(2) 2-Methylmaleate(4) Cyanate(1) 4-Hydroxymandelate(1) Methane(1)
4,6-Dihydroxyquinoline(1)
Pyruvate(101) 4-Hydroxybenzaldehyde(1)
Oxamate(1)
Fluoren-9-ol(1)
CoA(1) Acetoacetate(2)
Toluate(1) Oxaloacetate 4-methyl ester(2) Cyclic amide(1)
D-Glycerate(1)
4-Cresol(1) N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole(1)
alpha-Ribazole(1)
Allysine(1) Deoxyinosine(1) Itaconate(1) o-Cresol(1)
CO2
4-Dedimethylamino-4-oxo-anhydrotetracycline(1) 4-Hydroxyphenylacetate(1) Carbamate(1)
5-Amino-6-(5'-phosphoribosylamino)uracil(1) Malate(1)
Linamarin(1)
Phthalate(1)
Fluorene(5)
1-Formyl-2-indanone(1) Succinate(1)
(R)-Mandelate(2)
UDPapiose(1) cis-2-Hydroxy cinnamate(2)
Benzoate(1)
D-Nopaline(1)
D-Ribonate(1)
Galactitol(1)
Indanone(1) 2-Formyl-1-indanone(1)
Ribitol(1)
Mandelonitrile(1)
Indan-1-ol(1) L-Adrenaline(1) Resorcinol(1)
4-Nitrophenol(1)
Benzaldehyde(2)
(-)-Carvone(2)
2-Coumarate(1)
L-Noradrenaline(1) 3,4-Dihydroxymandelaldehyde(1)
Deoxyribose(1)
Hyponitrite(1)
Propan-2-ol(1) 6-Phospho-5-dehydro-2-deoxy-D-gluconate(2) Taxiphyllin(1) Ethanolamine phosphate(2) 4-Oxoproline(1)
D-Arabitol(1)
L-Histidinal(1)
3-Hydroxykynurenamine(1)
4,8-Dihydroxyquinoline(1)
Ecgonine methyl ester(1)
2-Nitrophenol(1)
Ecgonine(2)
Cocaine(1) Retronecine(1)
D-Mannuronate(1)
trans-Cinnamate(2)
Indolelactate(1)
Pseudouridine(1)
Sedoheptulose(1)
2-Methylserine(1)
UDP-L-rhamnose(1)
beta-Alanopine(1)
2-Hydroxyadipate(1)
4-Methylpentanal(1)
Formyl phosphate(1)
L-Homocitrulline(1)
Perillyl alcohol(1)
Propane-1,3-diol(1)
(-)-Isopiperitenone(1)
2-Hydroxybiphenyl(1)
Estradiol-17alpha(1)
Perillyl aldehyde(1)
5-Dehydroshikimate(1)
D-Galactonolactone(1)
N-Methyl-L-alanine(1)
N4-Phosphoagmatine(1)
2-Dehydro-L-idonate(1)
Sorbose 1-phosphate(1)
Xylitol 5-phosphate(1)
(R)-Propane-1,2-diol(1)
(S)-Propane-1,2-diol(1)
GDP-6-deoxy-D-talose(1)
L-Fucose 1-phosphate(1)
L-Tyrosyl-L-arginine(1)
N-Glucosylnicotinate(1)
N-Hydroxy-L-tyrosine(1)
dTDP-D-galacturonate(1)
(R,R)-Butane-2,3-diol(1)
(S,S)-Butane-2,3-diol(1)
3-Dehydro-L-threonate(1)
4-Phospho-L-aspartate(1)
2-Aminoethylphosphocholate(1)
5-Hydroxymethyluracil(1)
5-Phosphoribosylamine(1)
5beta-Cholestan-3-one(1)
Aryl beta-D-glucoside(1)
D-Glucono-1,4-lactone(1)
Farnesyl triphosphate(1)
GDP-6-deoxy-D-mannose(1)
N5-Methyl-L-glutamine(1)
Phosphoguanidinoacetate(1) (S)-1-Phenylethanol(1) dTDP-6-deoxy-L-talose(1)
(R)-1-Aminopropan-2-ol(1)
10-Formyldihydrofolate(1)
2,2'-Iminodipropanoate(1)
3-Phosphonooxypyruvate(1)
5alpha-Cholestan-3-one(1)
ADPribose 2'-phosphate(1)
L-Glutamyl 5-phosphate(1)
N-Adenylylanthranilate(1)
dTDP-6-deoxy-L-mannose(2)
4-Phospho-D-erythronate(1)
N-Glycoloyl-neuraminate(1)
N2-Succinyl-L-ornithine(1)
4,5beta-Dihydrocortisone(1)
D-4'-Phosphopantothenate(1)
Deoxy-5-methylcytidylate(1) Butanoyl-CoA(9)
(S)-3-Hydroxyisobutyrate(1) 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole(1)
Deoxy-ribose 1-phosphate(1)
4,5alpha-Dihydrocortisone(1)
7alpha-Hydroxycholesterol(1)
CDP-3,6-dideoxy-D-glucose(2)
(5S)-5-Amino-3-oxohexanoic acid(1)
3-(4-Hydroxyphenyl)lactate(1)
N-Adenylyl-L-phenylalanine(1)
alpha-D-Glutamyl phosphate(1)
alpha-D-Xylose 1-phosphate(1)
(S)-4-Hydroxymandelonitrile(1)
2,6-Dioxo-6-phenylhexanoate(1)
4-Hydroxyphenylacetonitrile(2)
7-Hydroxycholest-4-en-3-one(1)
N-(Carboxymethyl)-D-alanine(1)
(S)-3-(Imidazol-5-yl)lactate(1) Thymine(1) 3-Hydroxy-L-kynurenine(2) 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide(1) 5'-Phosphoribosylglycinamide(1) Xanthurenic acid(2) 6F-alpha-D-Galactosylsucrose(1)
L-2-Amino-6-oxoheptanedioate(2)
D-Galacturonate(3)
beta-L-Arabinose 1-phosphate(1)
Anhydrotetracycline(1)
Amino group donor(1)
5-Dehydro-2-deoxy-D-gluconate(1)
(R)-3-(4-Hydroxyphenyl)lactate(1)
4-(beta-D-glucosyloxy)benzoate(1)
5'-O-beta-D-Glucosylpyridoxine(1)
5-Hydroxymethyldeoxycytidylate(1)
N2-(D-1-Carboxyethyl)-L-lysine(1)
(2,3-Dihydroxybenzoyl)adenylate(1)
1-Phospho-alpha-D-galacturonate(1)
ATP
5-Amino-4-imidazolecarboxyamide(1)
cis-1,2-Dihydrobenzene-1,2-diol(1)
CMP-3-deoxy-D-manno-octulosonate(1)
Indole-3-acetyl-beta-1-D-glucose(1)
N-Acetyl-L-glutamate 5-phosphate(1)
N2-(D-1-Carboxyethyl)-L-arginine(1)
N(alpha)-gamma-L-Glutamylhistamine(1)
trans-Cinnamoyl beta-D-glucoside(1) Piperideine(2) 5-Dehydro-4-deoxy-D-glucuronate(4)
5-Methyldeoxycytidine diphosphate(1)
N-(2,3-Dihydroxybenzoyl)-L-serine(1)
Cytochrome C(2)
Apocytochrome c(1)
N5-(L-1-Carboxyethyl)-L-ornithine(1) Heme(4) N6-[(Indole-3-yl)acetyl]-L-lysine(1)
Hemoglobin(3)
Globin(1)
trans-1,2-Dihydrobenzene-1,2-diol(1)
6-Lactoyl-5,6,7,8-tetrahydropterin(1)
dTDP-4-amino-4,6-dideoxy-D-glucose(1)
L-1-Pyrroline-3-hydroxy-5-carboxylate(2)
4-(3-Methylbut-2-enyl)-L-tryptophan(1)
Androst-5-ene-3beta,17beta-diol(1)
CDP-4-dehydro-3,6-dideoxy-D-glucose(1)
Cetraxate benzyl ester(1)
Benzyl alcohol(1)
Cetraxate(1)
cis-1,2-Dihydronaphthalene-1,2-diol(1)
Prekinamycin(1)
1-Deoxy-D-altro-heptulose 7-phosphate(1)
alpha-Oxo-benzeneacetic acid(1)
5'-Phosphoribosyl-N-formylglycinamide(1)
Kinamycin D(1)
(R)-Lactaldehyde(1)
(S)-Lactaldehyde(1)
N2-(D-1,3-Dicarboxypropyl)-L-arginine(1) 1-Hydroxy-2-naphthaldehyde(1) L-threo-3-Phenylserine(1)
D-Fuconate(3)
Propanal(3)
Phenanthrene-3,4-diol(3)
3-Methyl-cis,cis-hexadienedioate(10)
2-Carboxybenzaldehyde(1)
(3E)-4-(2-Carboxyphenyl)-2-oxobut-3-enoate(2) Salicylaldehyde(1) Naphthalene-1,2-diol(3)
1,2-Bis(4-hydroxyphenyl)-2-propanol(2) 4'-Hydroxyacetophenone(1) 3-Isopropylbut-3-enoic acid(1) trans-beta-D-Glucosyl-2-hydroxycinnamate(2) Phenyl acetate(1) Benzylsuccinate(1)
Toluene(1)
Tropine(1) 3,5-Dihydroxyphenylglyoxylate(1)
Phosphoribosyl-AMP(4)
1-O,6-O-Digalloyl-beta-D-glucose(1)
1-O-Galloyl-beta-D-glucose(1)
3-Amino-4,7-dihydroxy-8-chlorocoumarin(1)
3-Isopropylbut-3-enoyl-CoA(1)
3,5-Dihydroxyphenylacetyl-CoA(1)
2-Aminophenol(4)
Aminoacetone(1)
Atropine(2) Chlorobiocic acid(1)
3-Hydroxyanthranilate(5) Threonate(1)
Cholesteryl-beta-D-glucoside(1)
5-Formiminotetrahydrofolate(1)
10-Formyltetrahydrofolate(3) 7-O-Acetylsalutaridinol(1)
Salidroside(1)
5'-Phospho-D-1-ribulosylformimine(1)
Thebaine(1)
4-Hydroxyphenyl acetate(1) Tetrahydrofolate(1)
4-O-beta-D-Glucosyl-4-hydroxycinnamate(1)
6-Acetyl-D-glucose(1)
5-Amino-6-(5'-phosphoribitylamino)uracil(1)
Glycolaldehyde(1)
Nicotinamide(1) Nicotinate(1)
(+)-cis-3,4-Dihydrophenanthrene-3,4-diol(1)
(4S,5S)-4,5-Dihydroxy-2,6-dioxohexanoate(1) Cholesterol(2) 1D-myo-Inositol 1,3,4,6-tetrakisphosphate(1)
N-Acetyl-alpha-D-glucosamine 1-phosphate(1)
4-Hydroxyphenylethanol(1)
D-Gluconolactone(1)
(1S,2S)-1,2-Dihydronaphthalene-1,2-diol(1)
D-Glucose(27)
beta-D-Fructose(1)
Retinol(2) 17alpha,20alpha-Dihydroxypregn-4-en-3-one(1)
1F-beta-D-Fructosylsucrose(1) 3-Dimethylallyl-4-hydroxybenzoate(1)
1D-myo-Inositol 3,4,5,6-tetrakisphosphate(1) 3-Methoxyanthranilate(1) 3alpha,7alpha-Dihydroxy-5beta-cholestanate(1)
4-Amino-2-methyl-5-phosphomethylpyrimidine(1)
UDP-N-acetyl-2-amino-2-deoxy-D-glucuronate(1)
Toluene-cis-dihydrodiol(1)
UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine(1)
1,6-Dihydroxycyclohexa-2,4-diene-1-carboxylate(1)
2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine(1)
2-(alpha-D-Galactosyl)-sn-glycerol 3-phosphate(1)
UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysine(1)
UDPMurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)(1)
alpha-D-Galactosyl-(1,1')-sn-glycerol 3-phosphate(1)
N6-(delta2-Isopentenyl)-adenosine 5'-monophosphate(1)
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate(1)
UDP-N-acetyl-6-(D-galactose-1-phospho)-D-glucosamine(1)
cis-4,5-Dihydroxycyclohexa-1(6),2-diene-1,2-dicarboxylate(1)
Choline sulfate(1)
ATP(97)
2-Amino-7,8-dihydro-4-hydroxy-6-(diphosphooxymethyl)pteridine(1)
alpha-D-Galactosyl-1,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosamine(1)
(6S)-6-beta-Hydroxy-1,4,5,6-tetrahydronicotinamide-adeninedinucleotide(1)
UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate(1)
UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine(1)
alpha-N-Acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine(1) 4-Hydroxy-L-threonine(1)
3-Aminopropane-1,2-diol(1)
24,25-Dihydrolanosterol(1)
(5-Hydroxyimidazole)-4-acetate(1)
17alpha-Hydroxypregnenolone(1)
16alpha-Hydroxydehydroepiandrosterone(1)
16alpha-Hydroxyandrost-4-ene-3,17-dione(1)
Estriol(1)
Dhurrin(1)
Hydroxyacetone(1)
19-Hydroxyandrost-4-ene-3,17-dione(1)
19-Oxoandrost-4-ene-3,17-dione(1)
2-Hydroxyestrone(1)
16alpha-Hydroxyestrone(1)
2-Hydroxyestradiol-17beta(1)
Semiquinone(1)
D-Ribitol(1)
D-Glucuronate 1-phosphate(1)
Cholesterol-5beta,6beta-epoxide(3)
cis-Phytoene(1)
Phytyl diphosphate(1)
3alpha,7alpha,26-Trihydroxy-5beta-cholestane(1) 3-Hydroxy-2-methylpropanoyl-CoA(1)
3-Hydroxy-2-methylpropanoate(1) 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-al(1)
Retinyl palmitate(2) 3-D-Glucuronosyl-N2,6-disulfo-beta-D-glucosamine(1) 3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane(1)
7alpha-Hydroxy-5beta-cholestan-3-one(1)
3alpha,7alpha-Dihydroxy-5beta-cholestane(1) beta-Lactam(3)
3-Methyl-2-oxobutanoic acid(3)
6-Aminopenicillanate(1) Dihydropteroate(1)
Benzoyl phosphate(1)
Coniferin(3) 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one(1) Estradiol-17beta(1) Coniferyl alcohol(4)
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane(1) O-Phospho-4-hydroxy-L-threonine(1)
Chlorogenate(1)
Orthophosphate(4)
7alpha-Hydroxycholest-4-en-3-one(1)
Quercetin3-O-beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside(1)
7alpha,12alpha-Dihydroxycholest-4-en-3-one(2)
Caffeate(1) 2-Phytyl-1,4-naphthoquinone(1)
Adenylyl-[L-glutamate:ammonia ligase (ADP-forming)](1)
[L-Glutamate:ammonia ligase (ADP-forming)](1)
Amino acid(Arg-)(1) Acetaldehyde(2)
17alpha,21-Dihydroxy-5beta-pregnane-3,11,20-trione(1) Desmosterol(1)
Phosphodimethylethanolamine(1)
UDP-sugar(1)
Sugar 1-phosphate(1)
4-Nitrophenyl phosphate(1) Iron(1)
(R)-4'-Phosphopantothenoyl-L-cysteine(1)
Pantetheine 4'-phosphate(1)
Urocortisone(1) 2-Amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine(1)
5-Phospho-alpha-D-ribose 1-diphosphate(1)
2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine(1)
Anapheline(1)
Urocortisol(1) D-Glucosamine 6-phosphate(5)
Nicotinate D-ribonucleotide(1)
Methylglyoxal(1)
Cortolone(1) 3-Carboxy-4-methyl-2-oxopentanoate(1)
Pelletierine(1)
Androst-4-ene-3,17-dione(1)
alpha-D-Ribose 1-phosphate(2)
3-Deoxy-D-manno-octulosonyl-lipid IV(A)(1) Cortol(1) Nicotinamide D-ribonucleotide(1)
4-Coumaroyl-CoA(1)
Di[3-deoxy-D-manno-octulosonyl]-lipid IV(A)(1) 4-Methyl-2-oxopentanoate(1)
2-Deoxy-D-glucose 6-phosphate(1)
2-Deoxy-D-glucose(1)
N-Ribosylnicotinamide(1) 17alpha,21-Dihydroxypregnenolone(1)
UDP-2,3-bis(3-hydroxytetradecanoyl)glucosamine(1) CDPcholine(1)
Maltol(1)
Nicotinate D-ribonucleoside(1)
2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate(1) 11-Deoxycortisol(1) Transferrin[Fe(II)]2(1)
Caffeoyl-CoA(1)
Apotransferrin(1)
2-Phosphoglycolate(1)
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate(1) 11beta,17alpha,21-Trihydroxypregnenolone(1) Thymidine(1)
2-Methyl-3-oxopropanoate(1)
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate(1)
Apoferritin(1)
21-Deoxycortisol(1) Transferrin[Fe(III)]2(1)
Sinapoyl-CoA(1) 17alpha,20alpha-Dihydroxycholesterol(1) Glutaryl-CoA(1)
Hydroxymethylphosphonate(1) 20alpha-Hydroxycholesterol(1) alpha-D-Galactose 1-phosphate(1)
Cinnamoyl-CoA(1)
Arbutin 6-phosphate(1)
20alpha,22beta-Dihydroxycholesterol(1) D-Sorbitol(1)
Phosphonoacetaldehyde(1)
Phenylacetyl-CoA(1) 2-Dehydropantoate(1)
Phosphoenolpyruvate(15)
Quercetin 3-sulfate(1)
L-Xylulose 1-phosphate(1) 22beta-Hydroxycholesterol(1) 4-Methyl-5-(2-phosphoethyl)-thiazole(1)
Nicotine(1) Estradiol-17beta 3-glucuronide(1)
Glyceraldehyde 3-phosphate(1)
2-(alpha-Hydroxyethyl)thiamine diphosphate(1) Thiamin diphosphate(3)
alpha-D-Glucose 1,6-bisphosphate(1)
Vestitone(1) 16-Glucuronide-estriol(1)
Laminaribiose(1)
Biochanin A(1) Urate-3-ribonucleoside(1)
D-Sedoheptulose 7-phosphate(1)
1-Hexadecanol(1) L-2-Aminoadipate adenylate(1)
Glycerone(1)
Formononetin(1) Imidazole lactate(1)
D-Erythrose 4-phosphate(1)
Cinnamaldehyde(1) D-Fructose 6-phosphate(46)
3,4-Dihydroxyphenylethyleneglycol(1)
Sedoheptulose 7-phosphate(2)
CoA-glutathione(1) 3,4-Dihydroxymandelate(1)
D-Glyceraldehyde(1)
N-Acetylserotonin(1)
Glycerol 1-phosphate(2)
N-Methylnicotinate(1)
3-Hydroxyphenylacetate(1) D-Glucose 1,6-bisphosphate(1)
7,8-Diaminononanoate(1)
Phenyllactate(1) Acetyl phosphate(2)
6-Carboxyhexanoyl-CoA(2)
Phenylpropanoate(1) Thiamin(3)
8-Amino-7-oxononanoic acid(1)
5-(2-Hydroxyethyl)-4-methylthiazole(1)
19-Hydroxytestosterone(2)
Quercetin 3,3'-bissulfate(1)
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate(1)
6-Hydroxyindolelactate(1)
Glycerol(3)
4-Amino-5-hydroxymethyl-2-methylpyrimidine(1)
Quercetin 3,4'-bissulfate(1)
CMP-2-aminoethylphosphonate(1)
1-O-Sinapoyl-beta-D-glucose(1)
D-Tagatose 6-phosphate(2)
L-Glutamyl 1-phosphate(1)
3-beta-D-Galactosyl-sn-glycerol(1) Galactose(1)
(R)-3-Amino-2-methylpropanoate(1)
(L-Seryl)adenylate(1)
Lactose 6-phosphate(1)
Lactose(6)
N-D-Ribosylpyrimidine(1)
1-alpha-D-Galactosyl-myo-inositol(1)
N-Methylethanolamine phosphate(1)
Luteolin 7-O-beta-D-diglucuronide(1)
2-Amino-5-oxohexanoate(1)
3',4',5-Trihydroxy-3,7-dimethoxyflavone(1)
Phenylethyl alcohol(1)
1-Deoxy-D-xylulose 5-phosphate(1)
D-Ribose(3)
Pyrimidine 5'-nucleotide(1)
Pyrimidine(1)
1F-alpha-D-Galactosylraffinose(1)
UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine(1)
Butanal(1)
6-(D-Glucose-1-phospho)-D-mannosylglycoprotein(1)
D-Mannosylglycoprotein(1)
Salicin 6-phosphate(1)
2-(Hydroxymethyl)phenol(1)
beta-Alanyl-L-arginine(1)
Acacetin(1)
D-Galactose(5)
(24R,24'R)-Fucosterol epoxide(1)
Luteolin(1)
Nebularine(1)
Purine(1)
Melibiitol(1)
17alpha-Hydroxyprogesterone(1)
Scopolin(1)
16-Epivellosimine(2)
Calycosin(1)
10-Formyltetrahydrofolyl L-glutamate(1)
Melatonin(2)
N2-Succinyl-L-glutamate 5-semialdehyde(1)
1-Methyladenosine(1)
Geissoschizine(2)
1-Methyladenine(1)
myo-Inositol(5)
L-Dopachrome(6)
N-(omega)-Hydroxyarginine(1)
Tauropine(1)
L-Arginine phosphate(1)
Taxifolin(1)
Ergosterol(3) Propane-1-ol(1) Medicarpin(2) 2-Hydroxybutanoic acid(1) Pinosylvin(1) dTDP(18) Psychosine(1) Acetyl adenylate(1) Lauroyl-CoA(1) Pentosans(1) Rosmarinate(1) dTDP-D-glucuronate(1) Thioacetate(1) Stizolobate(1) Biotinyl-CoA(1) Stizolobinate(1) Octanoyl-CoA(1) 2-Oxo-3-hydroxy-4-phosphobutanoate(1) 3-Ethylmalate(1) Anabasine(1) CoA-disulfide(1)
Acetyl-maltose(1)
4-Sulfobenzoate(1)
Cinnamyl alcohol(1)
Precorrin 2(1)
Uroporphyrin III(1)
2'-Hydroxydaidzein(1)
2-Isopropylmalate(3)
O-Feruloylquinate(1)
Pyrimidodiazepine(1)
Tetradecanoyl-CoA(1)
6-Carboxyhexanoate(1)
Coniferyl aldehyde(1)
Dihydrobiochanin A(1)
N-Acetoxyarylamine(1)
N-Acetyl-L-leucine(1)
N-Feruloyltyramine(1)
Psychosine sulfate(1)
2-trans-Hexadecenal(1)
Cortisol 21-acetate(1)
Cortisol 21-sulfate(1)
Sinapoyl-(S)-malate(1)
Dihydromyricetin(1)
1-Methylnicotinamide(1)
1-Sinapoyl-D-glucose(1)
2'-Hydroxyformononetin(1)
2-Caffeoylisocitrate(1)
3-Dehydrosphinganine(1)
3-cis-Dodecenoyl-CoA(3)
4-Coumaroylshikimate(1)
N-Caffeoylputrescine(1)
2,3-Dihydrogossypetin(1)
2-Methylcrotanoyl-CoA(1)
3-Methylcrotonyl-CoA(2)
N-Benzoylanthranilate(1)
N-Phosphotaurocyamine(1)
Oxidized trypanothione(1)
CDP-N-methylethanolamine(1)
Luteolin 7-O-glucuronide(1)
S-Acetylthioethanolamine(1)
2'-Hydroxydihydrodaidzein(1)
3,4',5-Trihydroxystilbene(1)
6''-O-Malonyl-biochanin A-beta-D-glucoside(1)
Sphingosyl-phosphocholine(1)
Bis-gamma-glutamylcystine(1)
1-O-Methyl-myo-inositol(1)
3-O-Methyl-myo-inositol(1)
N2,N5-Dibenzoyl-L-ornithine(1)
Adenosine 5'-phosphoramidate(1)
Quercetin 3,3',7-trissulfate(1)
Quercetin 3,4',7-trissulfate(1)
Luteolin 7-O-beta-D-glucoside(1)
N6-Acetyl-N6-hydroxy-L-lysine(1)
3-Hydroxy-4-methylanthranilate(1)
N-Acetyl-4-O-acetylneuraminate(1)
N-Acetyl-7-O-acetylneuraminate(1)
3'-Phosphoadenylyl sulfate(4)
N-Acetyl-9-O-acetylneuraminate(1)
Vitexin 2''-O-beta-D-glucoside(1)
alpha-N-Phenylacetyl-L-glutamine(1)
5-Methylthio-D-ribose 1-phosphate(2)
Isovitexin 2''-O-beta-D-glucoside(1)
5,7,4'-Trihydroxy-3'-methoxyflavone(1)
S-Adenosyl-4-methylthio-2-oxobutanoate(1)
3',4',5,7-Tetrahydroxy-3-methoxyflavone(1)
3',5-Dihydroxy-3,4',7-trimethoxyflavone(1)
N-(4-Guanidinobutyl)-4-hydroxycinnamide(1)
24-Methylene-5alpha-cholest-8-en-3beta-ol(1)
(3S,4S)-3-Hydroxytetradecane-1,3,4-tricarboxylate(1)
gamma-L-Glutamyl-L-cysteinyl-beta-alanine(1)
7-O-beta-D-Glucosyl-5,7,4'-trihydroxyflavone(1)
3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA(1)
(2S,3S)-2-Hydroxytridecane-1,2,3-tricarboxylate(1)
7-(5-Carboxyl-5-oxopentanyl)-aminocephalosporinate(1)
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoA(1)
7-O-(beta-D-apiofuranosyl-1,2-beta-D-glucosyl)-5,7,4'-trihydroxyflavone(1)
Luteolin7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide(1)
(S)-Cheilanthifoline(1)
6,7,12b,13e-Tetrahydro-4H-bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine(1)
3-Hydroxybenzoyl-CoA(1)
5'-Deoxyadenosine(1)
(S)-3-Hydroxyhexadecanoyl-CoA(2)
3-Oxopalmitoyl-CoA(1)
(S)-3-Hydroxytetradecanoyl-CoA(2)
3-Oxotetradecanoyl-CoA(1)
3-Oxododecanoyl-CoA(1)
(S)-Hydroxydecanoyl-CoA(2)
3-Oxodecanoyl-CoA(1)
(S)-Hydroxyoctanoyl-CoA(2)
3-Oxooctanoyl-CoA(1)
(S)-Hydroxyhexanoyl-CoA(2)
3-Oxohexanoyl-CoA(1)
Hexanoyl-CoA(1)
Decanoyl-CoA(1)
2-Methoxyestrone(1)
2-Methoxyestradiol-17beta(1)
4-Hydroxyphenylacetyl-CoA(1)
Biochanin A-beta-D-glucoside(1)
Ergosta-5,7,22,24(28)-tetraen-3beta-ol(1)
Phytosterol(1)
delta(L-2-Aminoadipyl)-L-cysteinyl-D-valine(3)
Homovanillate(1)
3-Methoxy-4-hydroxymandelate(1)
3-Methoxy-4-hydroxyphenylethyleneglycol(1)
4-Hydroxyphenylacetylglutamine(1)
4-Hydroxyphenylacetylglycine(1)
Phenylacetylglycine(1)
4-Hydroxycinnamyl aldehyde(1)
Sinapoyl aldehyde(1)
5-Hydroxyferulate(1)
Malonylapiin(1)
Quercetin 3-O-glucoside(1)
Rutin(1)
Eriodictyol(1)
5-Methoxyindoleacetate(1)
Precorrin 3A(1)
3-Mercaptolactate(1)
Methylimidazoleacetic acid(1)
3-Methoxyapigenin(1)
Cyanidin(1)
Leucocyanidin(1)
Dephospho-CoA
Arbutin(1) Phylloquinone(2)
Trypanothione(1)
(S)-Mevalonate(1)
Hexadimethrine bromide(1)
Cyclic 2,3-bisphospho-D-glycerate(1)
Sedoheptulose 1-phosphate(1)
L-Arabinose 1-phosphate(1)
UDP-N-acetyl-D-mannosaminouronate(1) Phenolic phosphate(1) Galactitol 1-phosphate(1) Shikimate 3-phosphate(1) L-Tagatose 6-phosphate(1) L-Fuculose 1-phosphate(2) 5-O-(1-Carboxyvinyl)-3-phosphoshikimate(1)
Biopterin(1) (4R,7R)-4-Isopropenyl-7-methyl-2-oxo-oxepanone(1) (3S,4R)-3,4-Dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate(1)
1,6-Dihydroxy-cis-2,4-cyclohexadiene-1-carboxylic acid(1)
Terephthalate(1)
L-Lyxonate(1)
L-Xylonate(1)
Quinolin-4-ol(1)
Methyl cinnamate(1) 3'-Keto-3'-deoxy-AMP(1) Ethyl cinnamate(1)
Propyl cinnamate(1)
ADP-D-glycero-D-manno-heptose(2)
2-(beta-D-Glucosyl)-sn-glycerol(1)
Biphenyl(1) 1-Guanidino-1-deoxy-scyllo-inositol(1) Aminophenol(1) cis-2,3-Dihydro-2,3-dihydroxybiphenyl(1) D-Glycero-D-manno-heptose 1-phosphate(1) Vanillate(1)
Pyridoxal(6) HO-(1)
Pyridoxamine(1) Phosphonate(1) Pyridoxal phosphate(2)
3-Amino-2-oxopropyl phosphate(1)
(3R)-6-Hydroxy-3-isopropenyl-heptanoate(2) 6-Pyruvoyltetrahydropterin(1) Fluoren-9-one(1)
1,6-Dihydroxy-5-methylcyclohexa-2,4-dienecarboxylate(1)
cis-1,2-Dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate(1)
Bilirubin(2)
L-Histidinol(1)
Aminoimidazole ribotide(2)
1,2-Dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate(1) 2(alpha-D-Mannosyl)-D-glycerate(1)
Bilirubin-glucuronoside(1)
Ascorbate(9)
Bilirubin beta-diglucuronide(1)
L-Urobilinogen(6)
3'-Keto-3'-deoxy-ATP(1) (1-Ribosylimidazole)-4-acetate(1)
2-(beta-D-Glucosyl)-sn-glycerol 3-phosphate(1) Prephytoene diphosphate(1) 1-Guanidino-1-deoxy-scyllo-inositol 4-phosphate(1) Presqualene diphosphate(1) D-Glycero-D-manno-heptose 1,7-bisphosphate(1) di-trans,poly-cis-Undecaprenyl diphosphate(1) Pyridoxamine phosphate(1) Myrcene(1) 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridinetriphosphate(4) Terpinolene(1) p-Xylene(1) Pinene(1) 4-Methylbenzyl alcohol(1) Pimaradiene(1) 3-Dimethylallyl-4-hydroxyphenylpyruvate(2) ent-Kaurene(1) L-Histidinol phosphate(1) (+)-Limonene(1) 2-(alpha-D-Mannosyl)-3-phosphoglycerate(1) (-)-beta-Pinene(1) 1-(5-Phosphoribosyl)imidazole-4-acetate(1) (-)-alpha-Pinene(1) Isopentenyl diphosphate(13) (+)-delta-Cadinene(1) p-Tolualdehyde(1) trans,trans,cis-Geranylgeranyl diphosphate(1) Nitrobenzene(1) (+)-Sandaracopimaradiene(1) Nitrosobenzene(1) (-)-Abietadiene(1) m-Xylene(1) Levopimaradiene(1) 3-Methylbenzaldehyde(1) Neoabietadiene(1) L-Valine(1) Palustradiene(1) 3-Dehydro-L-gulonate(1) Aphidicol-16-ene(1) m-Methylbenzoate(1) Aphidicol-15-ene(1) o-Xylene(1) Hexadecanoic acid(1)
Pentadecanal(1)
2-Methylbenzyl alcohol(1) Cembrene(1) 2-Methylbenzaldehyde(1) Taxa-4(5),11(12)-diene(1) o-Toluate(1) Vetispiradiene(1) 3-Methylbenzyl alcohol(1) (-)-Limonene(1) 14-Demethyllanosterol(1) Prenol(1) Limonene-1,2-epoxide(3) Casbene(1) dTDP-D-fucose(1) Pentalenene(1) 2-Amino-3-oxo-4-phosphonooxybutyrate(1) Trichodiene(1) 3-Hydroxy-1-indanone(1) Aristolochene(1) (+)-(3S,4R)-cis-3,4-Dihydroxy-3,4-dihydrofluorene(1) (-)-endo-Fenchol(1) 3,4-Dihydroxy-3,4-dihydro-9-fluorenone(2) Sabinene hydrate(1) Dibenzofuran(1) Neryl diphosphate(1) Dibenzo-p-dioxin(1)
Carbazole(1)
2-Methylpropanamine(1) (3S,6R)-6-Isopropenyl-3-methyl-2-oxo-oxepanone(1)
Indican(1)
(5R)-6-Hydroxy-5-isopropenyl-2-methylhexanoate(1) (4S,7R)-4-Isopropenyl-7-methyl-2-oxo-oxepanone(1)
Tetrahydrofolyl-[Glu](2)(1)
L-Xylulose(2) (3S)-6-Hydroxy-3-isopropenyl-heptanoate(2) (3S,6S)-6-Isopropenyl-3-methyl-2-oxo-oxepanone(1)
2'-Deoxy-5-hydroxymethylcytidine-5'-diphosphate(1)
(5S)-6-Hydroxy-5-isopropenyl-2-methylhexanoate(1) 4alpha-Methylcholesta-8-en-3beta-ol(2)
2'-Deoxy-5-hydroxymethylcytidine-5'-triphosphate(1)
Estrone glucuronide(1)
Testosterone glucuronide(1)
1-Diphosinositol pentakisphosphate(1)
(+)-(S)-Carvone(8)
(+)-trans-Carveol(1)
2-C-Methyl-D-erythritol 4-phosphate(1)
4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol(1)
4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol(1)
3-(3-Hydroxy-phenyl)-propanoic acid(1)
Quinate(1)
1D-myo-Inositol 1,4,5,6-tetrakisphosphate(1)
cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol(1)
dTDP-L-olivose(1)
dTDP-4-oxo-2,6-dideoxy-D-glucose(2)
Perillic acid(1)
dTDP-3-amino-3,6-dideoxy-D-glucose(1)
dTDP-4-oxo-2,6-dideoxy-L-mannose(2)
UDP-3-ketoglucose(1)
3-Cresol(1)
6-Methylsalicylate(1)
dTDP-3-amino-2,3,6-trideoxy-D-threo-hexopyranos-4-ulose(1)
trans-3-Hydroxycinnamate(1)
cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol(1)
N2-Acetyl-L-aminoadipate(1)
N2-Acetyl-L-aminoadipyl-delta-phosphate(1)
2,2-Bis(4-hydroxyphenyl)-1-propanol(2)
4-Ethylphenol(1)
1-(4'-Hydroxyphenyl)ethanol(1)
UDP-N-acetyl-D-galactosaminuronic acid(1)
dATP(1)
5,10-Methylenetetrahydrofolate(1)
D-Xylose(3)
dADP(1)
L-Arabinose(2)
Dihydrobiopterin(1)
Tetrahydrobiopterin(1)
HCO3-(1)
Glucose(1)
GDP-L-fucose(1)
Deoxyguanosine(1)
dGDP(1)
Xylitol(1)
Dihydrofolate(1)
(R)-Mevalonate(1)
5-Methyltetrahydrofolate(1)
N6-(L-1,3-Dicarboxypropyl)-L-lysine(1)
Acetoin(1)
Glutarate(1)
CDPglucose(2)
Folate(1)
L-Arabitol(1)
Nitric oxide(1)
Testosterone(1)
CDPethanolamine(1)
3-Phosphoglycerate(1) Luteoforol(1) N-Acetyllactosamine(1) Delphinidin(1) D-Arabinono-1,4-lactone(4) Leucodelphinidin(1) 2,4,6/3,5-Pentahydroxycyclohexanone(4) Pentahydroxyflavanone(1) UDP-N-acetylmuramoyl-L-alanyl-D-glutamate(1) Biotinyl-5'-AMP(1) Cortisol(2) (S)-3-Methyl-2-oxopentanoic acid(1)
2-Methylbutanal(1) Diacetyl(1)
3-Oxopropionyl-CoA(1) Squalene(3) (S)-2-Hydroxy-3-methyl-3-oxopentanoate(2) Cortisone(1) (R)-2,3-Dihydroxy-3-methylpentanoate(2) L-Idonate(1) Benzenamine sulfate(1) Mevaldate(1) dTDP-4-acetamido-4,6-dideoxy-D-glucose(1) CDPribitol(1) 3-Methoxy-4-hydroxyphenylacetate(1) D-Tagatose(1) 3-Ketosphingosine(1) Oxalureate(1) 1-Butanol(1) Naphthalene(1) 6-(3'-Triphosphoryl-1'-methylglyceryl)-7-methyl-7,8-dihydrobiopterin(1) 3',5'-Cyclic CMP(1) Malvidin 3-O-glucoside(1) Indole-3-ethanol(1)
(S)-cis-N-methylstylopine(1)
L-2-Aminoadipate(1)
Nonane-4,6-dione(1)
(-)-trans-Carveol(1)
N-Methylserotonin(1)
Ethylene(1)
S-1,5-Cyclohexadiene-1-carboxylate coenzymeA(5)
GDP-D-mannuronate(1) 3-Hydroxy-2-methylpyridine-5-carboxylate(1)
4-O-Methyl-myo-inositol(1)
D-Alanyl-D-alanine(1)
6-O-Methyl-myo-inositol(1)
N6-Hydroxy-L-lysine(1)
2,3',4,6-Tetrahydroxybenzophenone(1)
2-Oxoadipate(1)
Palmitoyl-CoA(1)
2,4,6-Trihydroxybenzophenone(1)
3-Hydroxy-2-methylpyridine-4,5-dicarboxylate(1) Inositol 1,2,3,4,5-pentakisphosphate(1)
(+)-Catechin(1)
Oxaloglutarate(1) D-myo-Inositol 1,2,4,5,6-pentakisphosphate(1)
Deacetoxycephalosporin C(1)
myo-Inositol hexakisphosphate(2) 5-(2'-Formylethyl)-4,6-dihydroxypicolinate(1)
Cephamycin C(1)
5-(3'-Carboxy-3'-oxopropyl)-4,6-dihydroxypicolinate(1)
Sinapoylcholine(1)
4-Hydroxyphthalate(1) 3-Hydroxybenzoate(1)
O-Carbamoyl-deacetylcephalosporin C(1)
6-Deoxy-L-galactose(2)
7a-Hydroxy-o-carbamoyl-deacetylcephalosporin C(1)
dTDP-4-oxo-3-methyl-2,6-dideoxy-beta-L-glucose(2)
Methyl-2-alpha-L-fucopyranosyl-beta-D-galactoside(1) Lacto-N-biose(1)
Toluene-4-sulfonate(1)
Delphinidin 3-O-glucoside(1)
4-Sulfobenzyl alcohol(1)
Methyl beta-D-galactoside(1) Pentan-2-one(1) Lacto-N-tetraose(1)
4-Sulfobenzaldehyde(1)
(R)-1,2-Epoxypropane(1) Butanoic acid(1)
3-Hydroxypimeloyl-CoA(4)
(R)-2-Hydroxypropyl-CoM(1)
3-Oxopimeloyl-CoA(1)
beta-D-Gal-(1->4)-D-Glc(1)
(S)-1,2-Epoxypropane(1) (S)-2-Hydroxypropyl-CoM(1)
(E)-11-Tetradecenoyl-CoA(1)
2-Mercaptoethanesulfonate(1)
(Z)-11-Tetradecenoyl-CoA(1) Tetrabromobisphenol A(4)
Bisphenol A(1) Adenosyl cobinamide(1)
Adenosyl cobyrinate hexaamide(1)
Hydrobromic acid(1) Benzoyl acetyl-CoA(1) Propene(1) Products of ATP breakdown(1)
Soyasaponin I(1)
3-Methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one(1)
Fluoroacetate(1)
(S)-2,3-Epoxysqualene(8) Zymosterol(2)
Raucaffricine(1)
Vomilenine(1)
alpha-L-Rhamnopyranosyl-(1->2)-beta-D-galactopyranosyl-(1->2)-beta-D-glucuronopyranoside(1) 1-O-Sinapoyl beta-D-glucoside(1)
1,2-Bis-O-sinapoyl-beta-D-glucoside(1)
ProteinN-(alpha-D-glucosyl)3-(alpha-D-mannosyl)8-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine(4)
alpha-D-Mannosyl-1,6(alpha-D-mannosyl-1,3)-alpha-D-mannosyl-1,6(alpha-D-mannosyl-1,3)-beta-D-mannonyl-1,4-N-acetyl-beta-D-glucosaminyl-1,4-N-acetyl-D-glucosaminyl-Asn(1)
Cephalosporin C(1)
Estradiol-17beta 3-sulfate(1) ProteinN-(N-acetyl-D-glucosaminyl-(alpha-D-mannosyl)2-beta-D-mannosyl-diacetylchitobiosyl)-L-asparagine(1)
2-Methoxyestrone 3-sulfate(1) sn-Glycero-3-phosphocholine(1)
Tubulosine(1)
Nicotyrine(1) alpha-D-Mannosyl-1,6(alpha-D-mannosyl-1,3)-alpha-D-mannosyl-1,6(N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,3)-beta-D-mannonyl-1,4-N-acetyl-beta-D-glucosaminyl-1,4-N-acetyl-D-glucosaminyl-Asn(1)
2-Methoxyestradiol-17beta 3-sulfate(1)
Cephaeline(1)
Emetine(1)
Fluoride(1)
Ankorine(2) Nucleoside diphosphate(1)
Cyanidin 3-O-rutinoside(1)
Nucleotide(1)
D-Cathinone(1)
Sinapate(1)
Diphospho-myo-inositol polyphosphate(1)
Naringenin 7-O-beta-D-glucoside(1)
myo-Inositol polyphosphate(1)
EPA(1) (2R)-2-Phospho-3-sulfolactate(1)
Choline phosphate(1)
Genistein 7-O-beta-D-glucoside(1)
(2R)-3-Sulfolactate(1)
Deacetylcephalosporin C(1) Isoflurophate(1)
Acetylcholine(1)
Afzelechin(1)
Choline(2)
3-(4-Methylpent-3-en-1-yl)-pent-2-enedioyl-CoA(2)
(-)-Epicatechin(1)
4-Acetamidobutanoyl-CoA(1)
Naringin(1)
Diisopropyl phosphate(1)
7-Methyl-3-oxooctanoyl-CoA(1)
4-Aminobutanoyl-CoA(1)
Quercitrin(1) Cyclohex-1-ene-1-carboxyl-CoA(2)
Acetate(1)
L-Rhamnose(3) 2-Protocatechoylphloroglucinolcarboxylate(1)
Benzylsuccinyl-CoA(1)
Quercetin(1)
E-Phenylitaconyl-CoA(2)
N(alpha)-Benzyloxycarbonyl-L-leucine(1)
Benzoylsuccinyl-CoA(1) Phorbol 13-butanoate(1) Apigenin 7-(6''-malonylglucoside)(1) (R)-3-Methyl-2-oxobutanoate(1)
L-Leucine(2)
4-Methylumbelliferyl acetate(1)
4-Methylumbelliferone(1)
N-Acetyl-D-galactosaminoglycan(1)
D-Galactosaminoglycan(1)
Citrate (pro-3S)-lyase (acetyl form)(1)
Citrate (pro-3S)-lyase (thiol form)(1)
5-(4-Acetoxybut-1-ynyl)-2,2'-bithiophene(1)
5-(4-Hydroxy-but-1-ynyl)-2,2'-bithiophene(1)
Kaempferide(1)
5-(3,4-Diacetoxybut-1-ynyl)-2,2'-bithiophene(1)
5-(3-Hydroxy-4-acetoxybut-1-ynyl)-2,2'-bithiophene(1)
Myricetin(1)
UDP-3-O-(3-hydroxytetradecanoyl)-N-acetylglucosamine(1)
UDP-3-O-(3-hydroxytetradecanoyl)-D-glucosamine(1)
Quercetin 3-(2G-xylosylrutinoside)(1)
N-Acetyl-D-galactosamine 6-phosphate(1)
D-Galactosamine 6-phosphate(1)
N-Acetylpuromycin(1)
Puromycin(1)
17-O-Acetylnorajmaline(1)
Norajmaline(1)
Phorbol 12,13-dibutanoate(1)
Tricetin(1)
Prunetin(1)
Caffeic aldehyde(1)
2-Methoxy-estradiol-17beta 3-glucuronide(1)
2-Methoxyestrone 3-glucuronide(1)
(S)-3-Sulfolactate(1)
(24R)-24-Methylcycloarta-8,25-dien-3-beta-ol(1)
Syringetin(1)
dTDP-3-methyl-4-oxo-2,6-dideoxy-L-glucose(1)
dTDP-L-mycarose(1)
dTDP-L-oleandrose(1)
Perillyl-CoA(2)
dTDP-D-mycaminose(1)
Apiforol(1)
(+)-Gallocatechin(1)
(-)-Epiafzelechin(1)
2'-Hydroxygenistein(1)
2'-Hydroxybiochanin A(1)
(-)-Epigallocatechin(1)
Pelargonidin 3-O-glucoside(1)
3-Oxo-4-methylpentanoic acid(1)
Phytosphingosine(1)
5-Hydroxyferuloyl-CoA(1)
5-Hydroxyconiferaldehyde(1)
5-Hydroxyconiferyl alcohol(1)
Caffeyl alcohol(1)
Kaempferol 3-O-glucoside(1)
dTDP-3-amino-2,3,6-trideoxy-C-methyl-D-erythro-hexopyranos-4-ulose(3)
dTDP-L-epivancosamine(1)
dTDP-5-dimethyl-L-lyxose(1)
Biochanin A 7-O-(6-O-malonyl-beta-D-glucoside)(1)
Kaempferol 3-O-beta-D-galactoside(1)
Apigenin 7-O-neohesperidoside(1)
Luteolin 7-O-neohesperidoside(1)
Laricitrin(1) Actinorhodine(1) Dihydrokalafungin(2)
[1] Handorf, T., Ebenh¨oh, O., Heinrich, R., Expanding Metabolic Networks: Scopes of Compounds, Robustness, and Evolution, J. Mol. Evol., 61:498-512, 2005
2,4-Dihydroxypteridine(1)
Sepiapterin(1)
L-3-Amino-isobutanoate(1)
4-Aminobenzenesulfonate(1)
5-Methylbarbiturate(1)
References
Pterin(1)
Pyrazole(1)
O-Acetyl-L-serine(1) Malonamoyl-CoA(1)
1,4-Cyclohexanedione(1)
The analysis of the scopes of single compounds reveals a hierarchy of metabolites which orders them according to their synthesizing capacity. This hierarchy also implies an ordering according to the complexity of the structure of the compounds, placing more complex compounds at the top while leaving more simple building blocks at the bottom. The overall structure of the graph is strongly influenced by the chemical composition of the metabolites. Typically, complex compounds which are composed of several different subunits can be split up, implying that their scopes are generally large and are superscopes of the scopes of all their subunits. In contrast complex compounds can generally not be formed from a single type of subunit. However, complex compounds may have small scopes if the necessary reactions are not present. This fact is responsible for the large number of sink nodes in the graph (74% of the connected nodes are sinks). So far our calculations concern the scopes of a metabolic network consisting of all known biochemical reactions. The same methods can directly be applied to the networks of specific organisms allowing for elucidation of their synthesizing capacities.
L-3-Aminobutyryl-CoA(1)
N2-Succinyl-L-arginine(1)
N-Acetyl-D-phenylalanine(1)
3-(Pyrazol-1-yl)-L-alanine(1)
4-Carboxy-4'-sulfoazobenzene(1)
Discussion
O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine(1)
N-Acetyl-L-histidine(1)
N-Malonylanthranilate(1)
2-Amino-3-oxobutanoate(1)
N-Acetyl-L-phenylalanine(1)
4-(beta-Acetylaminoethyl)imidazole(1)
2-Amino-5-oxocyclohex-1-enecarbonyl-CoA(1)
Trimethylamine(1)
3
3,5-Diiodo-4-hydroxyphenylpyruvate(1) 3,5-Diiodo-L-tyrosine(1)
Cobalt(1)
Sirohydrochlorin(1)
subscopes. A large in degree means that the corresponding scope is a subscope of many different superscopes. Systematic analysis of the graph reveals that 1191 out of 2922 nodes are isolated. Among the connected nodes 193 are sources (scopes that do not have superscopes) and 1279 are sinks (scopes that do not have subscopes). The nodes representing the scopes of ATP and Dephospho-CoA have the highest out-degrees (493 and 317) corresponding to the pronounced mushroom shaped structures at the top (Dephospho-CoA) and in the middle (ATP). The nodes for the scopes of CO 2 and NH3 have the highest in-degrees (63 and 57) and both are situated near the bottom of the graph.
Acceptor(1)
Siroheme(1)
Figure 1: Scope Hierarchy of the KEGG biochemical network. Nodes represent scopes and edges point from superscopes to their subscopes. The nodes for the scopes of ATP, Dephospho-CoA, CO 2 and NH3 are indicated.
Manganese(1)
Reduced acceptor(1)
Cobalt-precorrin 2(1)
